1. Field of the Invention
The present invention relates to the production of 1-octen-7-yne by hydrocoupling butadiene and vinyl acetylene.
2. Description of the Prior Art
1-Octen-7-yne is a useful chemical intermediate. Since olefinic and acetylenic bonds have different reactivities, this subject compound is useful for synthesis of bifunctional compounds, particularly compounds having terminally distributed functional groups. Illustrative of such compounds are 1,2-epoxy-7-octyne, 6-heptynoic acid, 1,2-dibromo-7-octyne and 2-cyano-1,7-octadiene.
Hydrodimerizing butadiene with formic acid and palladium catalyst is known. Wright in U.S. Pat. No. 3,732,328 issued May 8, 1973, prepares mixtures of octadienes by reacting butadiene in the presence of a palladium compound, a polar solvent, a reducing agent and a tertiary phosphine. Wright in U.S. Pat. No. 3,832,199, issued July 9, 1974, prepares mixtures of octadiene by reacting butadienes in the presence of a palladium compound, a non-polar solvent, a reducing agent and a tertiary phosphine. Wright in British Pat. No. 1,341,324 issued Dec. 9, 1973 discloses processes similar to above. Gardner et al, Tetrahedron Letters No. 2, pp. 163-164 (1972) discloses the production of mixtures of octadiene by reacting butadiene in the presence of palladium salts, or organic base, formic acid and a phosphine. Roffia et al, Journal of Organometallic Chemistry, 55 (1973) 405-407 utilizes a phoshpine-zero valent palladium complex catalyst in benzene in the presence of formic acid to dimerize butadiene.
Hydrodimerization of vinyl acetylene is not a known process.